


Same Mistakes

by itsangelpie



Category: Supernatural
Genre: F/M, Fluff and Angst, Mild Language, Possible Spoilers, Reader-Insert, Spoilers, Witch!Reader, gender neutral reader
Language: English
Status: Completed
Published: 2021-01-08
Updated: 2021-01-08
Packaged: 2021-03-12 13:14:41
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,358
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28636098
Author URL: https://archiveofourown.org/users/itsangelpie/pseuds/itsangelpie
Summary: With Chuck on a deadly mission and the entire of the world on the line, Dean Winchester turns to the one person he knowns that can help: you.
Relationships: Dean Winchester & You, Dean Winchester/You
Kudos: 17





	Same Mistakes

**Author's Note:**

> This was favorite scene in the entire episode, so this was a joy to write! Hope you all enjoy! <3
> 
> Pairing(s): Dean Winchester x Witch Reader!

You always did love the atmosphere of a good roadside diner.

It was always so warm and welcoming, serving everyone who had the pleasure of stepping inside. The servers always seemed to have a smile on their face, no matter the table, and it only shined brighter when you left them a generous tip for their always excellent service. Whether it was just a much-needed rest or a hearty plate of freshly-made food, there was something there for everyone. To you, the diner you were currently in was like a safe place from the darkness that the world carried outside of it. Nothing from your long, yet dangerous life as a 250-year-old witch was able to bother you here, and you found a comforting amount of pride in that fact.

Well, at least, you thought nothing of your long, yet dangerous life as a 250-year-old witch was able to bother you here.

But when the infamous Dean Winchester stepped inside what you considered your sanctuary, you weren’t so sure about that anymore. He only looks around the diner for a moment before his eyes catch yours, and both of your breaths catch in your throat.

You were just as breathtaking as he remembered, and he was just as ruggedly handsome as you recalled.

Neither of you broke eye contact, daring the other to look away first as he moved closer and closer to the table you resided at. He sat down across from you slowly, knowing that the last time you had seen each other was not as cordial as either of you would like to remember.

“You age pretty, Winchester,” you tell him, smiling lightly in victory when he finally breaks eye contact with you, trying to hide the faint blush that had appeared on his stubble-dusted cheeks.

However, being Dean Winchester, he always knew how to recover quickly.

“You’re one to talk, sweetheart,” he smirks, eyes filling with an unreadable emotion as he looks over you. “You don’t look a day over 100.”

The laughs this pulls from you warms his heart, momentarily making him discouraged with the fact there was no other way to defeat Chuck without what he was about to ask of you. Many say that everything the Winchester’s touch is eventually sentenced to death, either by affiliation, revenge of an enemy, or almost anything else you could think of. Unfortunately, so many people had proved that assumption right, and Dean wouldn’t know what to do with himself if you ended up being one of them.

“Before I ask why you’re here because I know the only reason you’d visit is for something you need from me, how’d you find me?”

Dean had to admit that one stung, but he deserved it along with the underlying bite in your usually smooth tone.

“I gotta keep tabs on what’s mine.” The look on Dean’s face as soon as he uttered the last two words told you that he knew that was the one of last things he had the right to say.

A sad chuckle leaves you, and it takes everything in you not to walk out right then and there. “I haven’t been yours for a long time, Winchester.”

Dean’s face immediately drops into one of sorrow, your continuous slights making him realize how unfair he was being. The last time you’d seen each other was a mess of shouting, tears, and pieces of each of your hearts lying broken on the ground beneath you. Now here he was, getting ready to ask you to put all of it behind you for his benefit.

“So, what’s up?” You ask, brushing past the onset of emotions you were feeling at the moment, hoping to get this conversation over with sooner than later. The faster you got through the conversation, the less time it gave for your heart to fall right back into his hands. “Who are you trying to get rid of now?”

“God.”

You look up from your now lukewarm coffee, thinking that he had to be joking. There was no question that the Winchester brothers had fought their fair share of big bads, though Chuck wasn’t one you expected to come up on the list.

But when Dean’s face doesn’t break out into that dazzling grin, the sides of his eyes crinkling in the best way, you knew he was completely serious. Watching you process the information just revealed to you, he couldn’t help but feel as if this was a lost cause.

What was stopping this situation to end up like the last one, this time instead of you breaking his heart by leaving in the middle of the night, you breaking his heart and spirit by possibly dying.

“You know I can’t do that, Dean,” you tell him after thinking for a few seconds. “It’s God. Even I don’t have the power to contain a force that big.”

“But we could try,” he exclaims, leaning towards you, determined eyes trained on your doubtful ones. “If we find a way––

“That’s a very big ‘if’,” you interrupt, but he keeps going.

“––he’d be gone for good. Imagine how better the world would be if that son of a bitch was gone. He’s let so many messed up things happen, and how does he repay us? By trying to erase it all and just start over. Who the hell is he to just throw the world away? There is so much life in this world, and he’s just willing to throw it all away because he feels like he failed.”

The amount of passion in Dean’s voice had rendered you speechless. Although you would never forget how much he cared for others (even if it didn’t seem like it all the time), being away from him all this time made this moment especially noble.

“But you know what? I’m not gonna let him. We’re not gonna let him. You, me, Sam, Cas, Jack, and whoever else wants to help, because the world deserves it.”

Dean then sat back in his chair, finished with his impromptu speech. He’s done and said all he could, and he would just have to hope that it would be enough to get you to join the fight.

You thought for another moment, before surprising him by laying one of your palms out on the table, book now closed and long forgotten. He carefully places his hand on top of yours and tries not to show how much he missed your soft touches. Tenderly squeezing his larger hand, you take a deep breath.

This would be dangerous.

You knew that if you decided to help them defeat Chuck, there was a possibility that someone wouldn’t make it out alive. What scared you, even more, is that there was a possibility that the someone that wouldn’t make it out alive was Dean.

No matter how broken your heart was the last time you spoke to him, he would always hold a place in it. No matter how hard you cried as you walked away from him for what you thought would be the last time, he would forever be yours and vice versa.

“Can I trust you?”

Dean knew you were asking about more than just defeating Chuck. After seeing each other today, you knew there were only a few deep conversations from melting right back into each other’s arms, which would require you to put your heart in the other’s heart again.

Although the last time ended up in a less than favorable outcome, the endgame you were about to face willed you to try it again. If you didn’t and something happened to him, you would never forgive yourself for not giving yourself another chance at true happiness.

Dean grabbed your hand in both of his now, once again looking straight into your eyes.

“I would never hurt you.”

He could have added ‘again’, but he didn’t need to. As the both of you sat here together, in your favorite roadside diner, the warming atmosphere wrapping around you, there was no question that either of you would make the same mistake of letting each other go again.

**Author's Note:**

> Kudos and comments are greatly appreciated! x


End file.
